# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nk1217
_database_code_depnum_ccdc_archive 'CCDC 2413116'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-05-20 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
_audit_creation_date             2025-05-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl I2, Cl4 Sb, C12 H14 N2'
_chemical_formula_sum            'C12 H14 Cl5 I2 N2 Sb'
_chemical_formula_weight         739.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

# start Validation Reply Form 
_vrf_PLAT230_nk1217              
;
PROBLEM: Hirshfeld Test Diff for    I1       --Cl1      .        8.1 s.u.  
RESPONSE: The anomalous Hirshfield Test value is an artefact of the
structure. There is no indicators that wrong atom type is assigned.
;
# end Validation Reply Form

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.2820(6)
_cell_length_b                   7.3356(3)
_cell_length_c                   19.7031(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.1010(10)
_cell_angle_gamma                90
_cell_volume                     2064.23(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      33.62
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.789
_shelx_estimated_absorpt_T_min   0.543
_exptl_absorpt_coefficient_mu    4.972
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0760 before and 0.0582 after correction.
The Ratio of minimum to maximum transmission is 0.8472.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.378
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35710
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.739
_diffrn_reflns_theta_min         1.760
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6518
_reflns_number_total             8239
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.802
_refine_diff_density_min         -1.860
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       0.00041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         8239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0087P)²+7.7988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5860(11)
 0.4140(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.15527(2) 0.77462(7) 0.61993(2) 0.01868(8) Uani 1 1 d . . . . .
I2 I -0.34749(3) 0.77197(8) 0.61902(3) 0.02693(10) Uani 1 1 d . . . . .
Sb1 Sb 0.24401(3) 0.77862(4) 0.64054(2) 0.01451(6) Uani 1 1 d . . . . .
Cl1 Cl 0.04157(10) 0.7771(2) 0.62337(8) 0.0327(3) Uani 1 1 d . . . . .
Cl2 Cl 0.24525(13) 0.99694(13) 0.54824(5) 0.02040(19) Uani 1 1 d . . . . .
Cl3 Cl 0.24894(13) 0.50609(12) 0.56082(5) 0.02107(18) Uani 1 1 d . . . . .
Cl4 Cl 0.41605(9) 0.7720(2) 0.64150(7) 0.0267(3) Uani 1 1 d . . . . .
Cl5 Cl 0.25265(14) 1.07959(15) 0.72320(5) 0.0285(2) Uani 1 1 d . . . . .
N1 N 0.4244(3) 0.2587(8) 0.6374(3) 0.0301(13) Uani 1 1 d . . . . .
H1 H 0.363520 0.253449 0.643855 0.036 Uiso 1 1 calc R U . . .
N2 N 1.0716(3) 0.2795(9) 0.6156(3) 0.0313(13) Uani 1 1 d . . . . .
H2 H 1.132012 0.276494 0.606774 0.038 Uiso 1 1 calc R U . . .
C1 C 0.4569(5) 0.2590(9) 0.5750(4) 0.0313(14) Uani 1 1 d . . . . .
H1A H 0.414958 0.253963 0.537541 0.038 Uiso 1 1 calc R U . . .
C2 C 0.5502(4) 0.2664(9) 0.5645(3) 0.0264(12) Uani 1 1 d . . . . .
H2A H 0.573696 0.267362 0.519458 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6115(4) 0.2726(8) 0.6182(3) 0.0223(11) Uani 1 1 d . . . . .
C4 C 0.5755(4) 0.2744(11) 0.6820(4) 0.0308(15) Uani 1 1 d . . . . .
H4 H 0.616042 0.281217 0.720206 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4807(5) 0.2662(11) 0.6910(4) 0.0379(18) Uani 1 1 d . . . . .
H5 H 0.455126 0.265784 0.735469 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7160(3) 0.2758(7) 0.6027(3) 0.0216(10) Uani 1 1 d . . . . .
H6A H 0.730870 0.167259 0.574851 0.026 Uiso 1 1 calc R U . . .
H6B H 0.729021 0.384557 0.574470 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7822(3) 0.2787(7) 0.6625(3) 0.0228(10) Uani 1 1 d . . . . .
H7A H 0.769760 0.170411 0.691059 0.027 Uiso 1 1 calc R U . . .
H7B H 0.768788 0.388208 0.690165 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8847(4) 0.2799(8) 0.6435(3) 0.0226(11) Uani 1 1 d . . . . .
C9 C 0.9151(4) 0.2636(9) 0.5765(3) 0.0285(13) Uani 1 1 d . . . . .
H9 H 0.871347 0.252213 0.540405 0.034 Uiso 1 1 calc R U . . .
C10 C 1.0103(4) 0.2645(10) 0.5639(3) 0.0310(15) Uani 1 1 d . . . . .
H10 H 1.032477 0.254487 0.518630 0.037 Uiso 1 1 calc R U . . .
C11 C 1.0435(5) 0.2988(10) 0.6797(4) 0.0348(17) Uani 1 1 d . . . . .
H11 H 1.087937 0.313918 0.715172 0.042 Uiso 1 1 calc R U . . .
C12 C 0.9508(5) 0.2965(10) 0.6933(4) 0.0322(15) Uani 1 1 d . . . . .
H12 H 0.930961 0.306790 0.739113 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.7453(4) . ?
I1 Cl1 2.8121(15) . ?
Sb1 Cl2 2.4234(9) . ?
Sb1 Cl3 2.5435(9) . ?
Sb1 Cl4 2.4577(13) . ?
Sb1 Cl5 2.7461(11) . ?
N1 H1 0.8800 . ?
N1 C1 1.315(9) . ?
N1 C5 1.326(10) . ?
N2 H2 0.8800 . ?
N2 C10 1.346(8) . ?
N2 C11 1.333(9) . ?
C1 H1A 0.9500 . ?
C1 C2 1.350(9) . ?
C2 H2A 0.9500 . ?
C2 C3 1.372(8) . ?
C3 C4 1.360(9) . ?
C3 C6 1.524(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(9) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.509(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.511(7) . ?
C8 C9 1.395(9) . ?
C8 C12 1.366(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.351(10) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 I1 Cl1 178.99(4) . . ?
Cl2 Sb1 Cl3 93.19(3) . . ?
Cl2 Sb1 Cl4 90.58(6) . . ?
Cl2 Sb1 Cl5 85.03(3) . . ?
Cl3 Sb1 Cl5 175.48(6) . . ?
Cl4 Sb1 Cl3 87.73(6) . . ?
Cl4 Sb1 Cl5 88.14(6) . . ?
C1 N1 H1 119.0 . . ?
C1 N1 C5 122.0(6) . . ?
C5 N1 H1 119.0 . . ?
C10 N2 H2 119.1 . . ?
C11 N2 H2 119.1 . . ?
C11 N2 C10 121.9(6) . . ?
N1 C1 H1A 120.3 . . ?
N1 C1 C2 119.5(7) . . ?
C2 C1 H1A 120.3 . . ?
C1 C2 H2A 119.6 . . ?
C1 C2 C3 120.9(6) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 C6 118.1(5) . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 C6 123.9(5) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(7) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 119.8(7) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C6 H6A 108.0 . . ?
C3 C6 H6B 108.0 . . ?
H6A C6 H6B 107.3 . . ?
C7 C6 C3 117.1(5) . . ?
C7 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.3(5) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C9 C8 C7 122.5(5) . . ?
C12 C8 C7 119.4(5) . . ?
C11 H11 Cl4 134.8(5) . 2_646 yes
C11 H11 Cl5 120.6(4) . 1_645 yes
C12 C8 C9 118.1(5) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(6) . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 120.2(6) . . ?
N2 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N2 C11 H11 120.5 . . ?
N2 C11 C12 118.9(7) . . ?
C12 C11 H11 120.5 . . ?
C8 C12 H12 118.8 . . ?
C11 C12 C8 122.3(7) . . ?
C11 C12 H12 118.8 . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_site_symmetry_2
_geom_contact_distance
_geom_contact_publ_flag
C11 Cl4 2_646 3.575(8) yes
C11 Cl5 1_645 3.498(7) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Cl5 0.88 2.57 3.258(5) 136.1 1_545 yes
N2 H2 Cl2 0.88 2.86 3.495(6) 130.8 1_645 yes
N2 H2 Cl3 0.88 2.54 3.217(6) 134.3 1_655 yes
C5 H5 Cl1 0.95 2.78 3.673(8) 156.4 2_546 yes
C6 H6A Cl2 0.99 2.73 3.627(5) 150.9 3_666 yes
C6 H6B Cl3 0.99 2.80 3.632(5) 141.8 3_666 yes
C11 H11 Cl4 0.95 2.84 3.575(8) 134.8 2_646 yes
C11 H11 Cl5 0.95 2.92 3.498(7) 120.6 1_645 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.4(10) . . . . ?
N2 C11 C12 C8 -1.8(12) . . . . ?
C1 N1 C5 C4 0.0(12) . . . . ?
C1 C2 C3 C4 -1.1(10) . . . . ?
C1 C2 C3 C6 178.4(6) . . . . ?
C2 C3 C4 C5 1.3(11) . . . . ?
C2 C3 C6 C7 -178.8(6) . . . . ?
C3 C4 C5 N1 -0.8(13) . . . . ?
C3 C6 C7 C8 179.4(4) . . . . ?
C4 C3 C6 C7 0.8(8) . . . . ?
C5 N1 C1 C2 0.2(11) . . . . ?
C6 C3 C4 C5 -178.2(7) . . . . ?
C6 C7 C8 C9 -5.3(8) . . . . ?
C6 C7 C8 C12 175.0(6) . . . . ?
C7 C8 C9 C10 -179.5(6) . . . . ?
C7 C8 C12 C11 -179.9(7) . . . . ?
C8 C9 C10 N2 0.5(11) . . . . ?
C9 C8 C12 C11 0.4(11) . . . . ?
C10 N2 C11 C12 2.5(11) . . . . ?
C11 N2 C10 C9 -1.8(11) . . . . ?
C12 C8 C9 C10 0.2(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5860(11)
2 0.4140(11)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nk1223
_database_code_depnum_ccdc_archive 'CCDC 2413118'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-05-14 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
_audit_creation_date             2025-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I2, Cl5 Sb, C13 H16 N2'
_chemical_formula_sum            'C13 H16 Cl5 I2 N2 Sb'
_chemical_formula_weight         753.08
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.3188(4)
_cell_length_b                   14.2431(3)
_cell_length_c                   9.9383(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2168.41(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    220.00
_cell_measurement_theta_max      30.97
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.764
_shelx_estimated_absorpt_T_min   0.422
_exptl_absorpt_coefficient_mu    4.735
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0766 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.7066.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.307
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29013
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.511
_diffrn_reflns_theta_min         2.443
_diffrn_ambient_temperature      220.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3053
_reflns_number_total             3744
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.00187(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0134P)²+1.8679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0478
_refine_ls_wR_factor_ref         0.0509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.64382(2) 0.34533(2) 0.43116(2) 0.04270(6) Uani 1 1 d . . . . .
Sb1 Sb 0.58004(2) 0.750000 0.39856(2) 0.03016(6) Uani 1 2 d S T P . .
Cl1 Cl 0.59424(5) 0.56664(5) 0.39349(7) 0.04548(15) Uani 1 1 d . . . . .
Cl2 Cl 0.72098(6) 0.750000 0.58025(8) 0.04044(19) Uani 1 2 d S T P . .
Cl3 Cl 0.69558(5) 0.750000 0.23591(8) 0.03187(16) Uani 1 2 d S T P . .
Cl4 Cl 0.47342(6) 0.750000 0.21119(9) 0.0422(2) Uani 1 2 d S T P . .
N1 N 0.31505(14) 0.58063(15) 0.0599(2) 0.0444(5) Uani 1 1 d . . . . .
H1 H 0.283331 0.629988 0.043479 0.053 Uiso 1 1 calc R U . . .
C1 C 0.34318(17) 0.52833(19) -0.0432(3) 0.0438(6) Uani 1 1 d . . . . .
H1A H 0.329309 0.545759 -0.131891 0.053 Uiso 1 1 calc R U . . .
C2 C 0.39178(16) 0.45006(18) -0.0201(3) 0.0393(6) Uani 1 1 d . . . . .
H2 H 0.411188 0.413052 -0.092510 0.047 Uiso 1 1 calc R U . . .
C3 C 0.41253(15) 0.42519(16) 0.1113(3) 0.0340(5) Uani 1 1 d . . . . .
C4 C 0.38295(17) 0.48178(19) 0.2149(3) 0.0439(6) Uani 1 1 d . . . . .
H4 H 0.396440 0.466827 0.304621 0.053 Uiso 1 1 calc R U . . .
C5 C 0.33414(19) 0.5593(2) 0.1863(3) 0.0496(7) Uani 1 1 d . . . . .
H5 H 0.313972 0.597831 0.256509 0.060 Uiso 1 1 calc R U . . .
C6 C 0.46344(17) 0.33785(17) 0.1402(3) 0.0456(6) Uani 1 1 d . . . . .
H6A H 0.482177 0.338378 0.234480 0.055 Uiso 1 1 calc R U . . .
H6B H 0.515870 0.336843 0.083712 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4101(2) 0.250000 0.1137(3) 0.0313(7) Uani 1 2 d S T P . .
H7A H 0.358491 0.250000 0.171914 0.038 Uiso 1 2 calc R U P . .
H7B H 0.390230 0.250000 0.020029 0.038 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I1 2.7156(4) 7_565 ?
Sb1 Cl1 2.6211(7) . ?
Sb1 Cl1 2.6211(7) 7_575 ?
Sb1 Cl2 2.8146(9) . ?
Sb1 Cl3 2.3970(8) . ?
Sb1 Cl4 2.4770(9) . ?
N1 H1 0.8700 . ?
N1 C1 1.338(4) . ?
N1 C5 1.325(4) . ?
C1 H1A 0.9400 . ?
C1 C2 1.360(4) . ?
C2 H2 0.9400 . ?
C2 C3 1.391(4) . ?
C3 C4 1.383(3) . ?
C3 C6 1.496(3) . ?
C4 H4 0.9400 . ?
C4 C5 1.364(4) . ?
C5 H5 0.9400 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 C7 1.517(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Sb1 Cl1 170.23(3) 7_575 . ?
Cl1 Sb1 Cl2 87.058(16) 7_575 . ?
Cl1 Sb1 Cl2 87.058(16) . . ?
Cl3 Sb1 Cl1 85.742(15) . . ?
Cl3 Sb1 Cl1 85.742(16) . 7_575 ?
Cl3 Sb1 Cl2 82.31(3) . . ?
Cl3 Sb1 Cl4 88.85(3) . . ?
Cl4 Sb1 Cl1 92.308(16) . 7_575 ?
Cl4 Sb1 Cl1 92.308(16) . . ?
Cl4 Sb1 Cl2 171.16(3) . . ?
C1 N1 H1 119.1 . . ?
C5 N1 H1 119.1 . . ?
C5 N1 C1 121.8(2) . . ?
N1 C1 H1A 119.9 . . ?
N1 C1 C2 120.2(3) . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C6 120.7(2) . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 C6 120.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.3(3) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C6 H6A 109.2 . . ?
C3 C6 H6B 109.2 . . ?
C3 C6 C7 111.8(2) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 C6 111.1(3) 7_565 . ?
C6 C7 H7A 109.4 7_565 . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 7_565 . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Cl2 0.87 2.31 3.136(2) 158.1 4_465 yes
N1 H1 Cl3 0.87 3.09 3.645(2) 123.9 4_465 yes
C2 H2 Cl1 0.94 3.01 3.724(3) 134.3 5_665 yes
C2 H2 Cl3 0.94 3.18 3.809(3) 126.2 3_645 yes
C5 H5 Cl3 0.94 2.83 3.533(3) 132.7 4_465 yes
C6 H6B Cl4 0.98 3.19 3.834(3) 125.1 3_645 yes
C7 H7A Cl2 0.98 2.75 3.645(3) 152.5 3_646 yes
C7 H7B Cl3 0.98 2.86 3.834(3) 170.8 3_645 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.5(4) . . . . ?
C1 N1 C5 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C6 178.0(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C6 C7 -70.5(3) . . . . ?
C3 C4 C5 N1 0.0(4) . . . . ?
C3 C6 C7 C6 178.60(17) . . . 7_565 ?
C4 C3 C6 C7 107.7(3) . . . . ?
C5 N1 C1 C2 1.0(4) . . . . ?
C6 C3 C4 C5 -177.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_101k
_database_code_depnum_ccdc_archive 'CCDC 2426309'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-05-22 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
_audit_creation_date             2025-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Cl5, I2, C12 H14 N2'
_chemical_formula_sum            'C12 H14 Bi Cl5 I2 N2'
_chemical_formula_weight         826.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

# start Validation Reply Form 
_vrf_PLAT971_2_101k              
;
PROBLEM: Check Calcd Resid. Dens.  0.76Ang From Bi1             3.48 eA-3  
RESPONSE: Residual density around heavy atom (Bi) due to features of absorbtion correction.
;
# end Validation Reply Form

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   7.3832(4)
_cell_length_b                   14.2708(7)
_cell_length_c                   19.6817(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2073.75(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5150
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      76.22
_cell_measurement_theta_min      3.83
_shelx_estimated_absorpt_T_max   0.460
_shelx_estimated_absorpt_T_min   0.169
_exptl_absorpt_coefficient_mu    45.972
_exptl_absorpt_correction_T_max  0.2981
_exptl_absorpt_correction_T_min  0.0979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1552 before and 0.0937 after correction.
The Ratio of minimum to maximum transmission is 0.3284.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.647
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13964
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.255
_diffrn_reflns_theta_min         3.826
_diffrn_ambient_temperature      100.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2032
_reflns_number_total             2254
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         3.506
_refine_diff_density_min         -1.789
_refine_diff_density_rms         0.295
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+4.5186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C8) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C7, C1, C2, N1, C3, C5, C6, C4, C8, C9, C12, C10, C11, N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: C1(0.5) H1(0.5) C2(0.5) H2(0.5) C3(0.5) C4(0.5) H4(0.5) C5(0.5)
 H5(0.5) N1(0.5) H1A(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5)
 C8(0.5) C9(0.5) H9(0.5) C10(0.5) H10(0.5) N2(0.5) H2A(0.5) C11(0.5) H11(0.5)
 C12(0.5) H12(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), N1(H1A), C9(H9), C10(H10), N2(H2A), C11(H11),
 C12(H12)
5.c Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,N1), C8(C9,C10,N2,C11,C12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.21913(5) 0.250000 0.64175(2) 0.02138(16) Uani 1 2 d S T P . .
I1 I 0.76454(6) 0.15482(3) 0.37594(2) 0.02510(17) Uani 1 1 d . . . . .
Cl2 Cl 0.4984(3) 0.250000 0.56113(11) 0.0261(4) Uani 1 2 d S T P . .
Cl3 Cl -0.0173(3) 0.250000 0.54664(10) 0.0251(4) Uani 1 2 d S T P . .
Cl4 Cl 0.2240(3) 0.06165(15) 0.63578(10) 0.0348(4) Uani 1 1 d . . . . .
Cl1 Cl -0.0872(4) 0.250000 0.72952(13) 0.0413(6) Uani 1 2 d S T P . .
C1 C 0.254(2) 0.5406(9) 0.4335(5) 0.024(3) Uani 0.5 1 d G U P A -1
H1 H 0.249527 0.581323 0.471662 0.028 Uiso 0.5 1 calc R U P A -1
C2 C 0.261(2) 0.4442(9) 0.4431(4) 0.029(4) Uani 0.5 1 d G . P A -1
H2 H 0.261445 0.418977 0.487746 0.035 Uiso 0.5 1 calc R U P A -1
C3 C 0.2674(17) 0.3846(6) 0.3872(7) 0.019(3) Uani 0.5 1 d G U P A -1
C4 C 0.2668(17) 0.4214(9) 0.3219(5) 0.025(3) Uani 0.5 1 d G . P A -1
H4 H 0.271151 0.380720 0.283728 0.030 Uiso 0.5 1 calc R U P A -1
C5 C 0.2597(19) 0.5179(9) 0.3123(4) 0.029(4) Uani 0.5 1 d G . P A -1
H5 H 0.259233 0.543066 0.267643 0.035 Uiso 0.5 1 calc R U P A -1
N1 N 0.253(2) 0.5775(6) 0.3681(7) 0.023(3) Uani 0.5 1 d G U P A -1
H1A H 0.248777 0.638512 0.362090 0.028 Uiso 0.5 1 calc R U P A -1
C6 C 0.2644(19) 0.2814(10) 0.4004(7) 0.025(3) Uani 0.5 1 d . . P A -1
H6A H 0.153972 0.267225 0.427008 0.030 Uiso 0.5 1 calc R U P A -1
H6B H 0.369572 0.266162 0.429576 0.030 Uiso 0.5 1 calc R U P A -1
C7 C 0.2683(18) 0.2158(10) 0.3402(7) 0.024(2) Uani 0.5 1 d . . P A -1
H7A H 0.160241 0.227938 0.311786 0.029 Uiso 0.5 1 calc R U P A -1
H7B H 0.376571 0.230167 0.312472 0.029 Uiso 0.5 1 calc R U P A -1
C8 C 0.2718(17) 0.1138(6) 0.3584(7) 0.020(3) Uani 0.5 1 d G U P A -1
C9 C 0.251(2) 0.0849(8) 0.4254(6) 0.028(4) Uani 0.5 1 d G . P A -1
H9 H 0.235227 0.130070 0.460390 0.034 Uiso 0.5 1 calc R U P A -1
C10 C 0.252(2) -0.0100(10) 0.4412(4) 0.039(5) Uani 0.5 1 d G . P A -1
H10 H 0.238082 -0.029754 0.486938 0.047 Uiso 0.5 1 calc R U P A -1
N2 N 0.275(2) -0.0760(6) 0.3900(7) 0.027(3) Uani 0.5 1 d G . P A -1
H2A H 0.276263 -0.136141 0.399935 0.033 Uiso 0.5 1 calc R U P A -1
C11 C 0.296(2) -0.0471(8) 0.3230(6) 0.028(4) Uani 0.5 1 d G . P A -1
H11 H 0.311759 -0.092268 0.287972 0.034 Uiso 0.5 1 calc R U P A -1
C12 C 0.295(2) 0.0478(10) 0.3072(4) 0.036(4) Uani 0.5 1 d G . P A -1
H12 H 0.308904 0.067556 0.261422 0.043 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl2 2.602(2) . ?
Bi1 Cl3 2.560(2) . ?
Bi1 Cl4 2.691(2) 7_565 ?
Bi1 Cl4 2.691(2) . ?
Bi1 Cl1 2.846(2) . ?
Bi1 Cl1 2.909(2) 6_657 ?
I1 I1 2.7167(9) 7_565 ?
C1 H1 0.9500 . ?
C1 C2 1.3900 . ?
C1 N1 1.3900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 C6 1.496(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 N1 1.3900 . ?
N1 H1A 0.8800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.51(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.498(16) . ?
C8 C9 1.3900 . ?
C8 C12 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 N2 1.3900 . ?
N2 H2A 0.8800 . ?
N2 C11 1.3900 . ?
C11 H11 0.9500 . ?
C11 C12 1.3900 . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Bi1 Cl4 87.86(4) . 7_565 ?
Cl2 Bi1 Cl4 87.86(4) . . ?
Cl2 Bi1 Cl1 98.15(8) . 6_657 ?
Cl2 Bi1 Cl1 179.79(8) . . ?
Cl3 Bi1 Cl2 95.42(7) . . ?
Cl3 Bi1 Cl4 88.69(4) . . ?
Cl3 Bi1 Cl4 88.69(4) . 7_565 ?
Cl3 Bi1 Cl1 166.44(8) . 6_657 ?
Cl3 Bi1 Cl1 84.37(8) . . ?
Cl4 Bi1 Cl4 174.76(8) 7_565 . ?
Cl4 Bi1 Cl1 91.80(4) 7_565 6_657 ?
Cl4 Bi1 Cl1 92.13(4) . . ?
Cl4 Bi1 Cl1 91.80(4) . 6_657 ?
Cl4 Bi1 Cl1 92.13(4) 7_565 . ?
Cl1 Bi1 Cl1 82.07(2) . 6_657 ?
Bi1 Cl1 Bi1 156.81(12) . 6_557 ?
C2 C1 H1 120.0 . . ?
C2 C1 N1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C6 117.7(11) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C6 122.2(11) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 N1 120.0 . . ?
N1 C5 H5 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C5 N1 C1 120.0 . . ?
C5 N1 H1A 120.0 . . ?
C3 C6 H6A 107.7 . . ?
C3 C6 H6B 107.7 . . ?
C3 C6 C7 118.4(12) . . ?
H6A C6 H6B 107.1 . . ?
C7 C6 H6A 107.7 . . ?
C7 C6 H6B 107.7 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.5(12) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C9 C8 C7 120.8(11) . . ?
C9 C8 C12 120.0 . . ?
C12 C8 C7 119.2(11) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
N2 C10 C9 120.0 . . ?
N2 C10 H10 120.0 . . ?
C10 N2 H2A 120.0 . . ?
C11 N2 C10 120.0 . . ?
C11 N2 H2A 120.0 . . ?
N2 C11 H11 120.0 . . ?
N2 C11 C12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C8 C12 H12 120.0 . . ?
C11 C12 C8 120.0 . . ?
C11 C12 H12 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 Cl4 0.95 2.94 3.804(9) 151.8 7_565 yes
C5 H5 Cl4 0.95 2.61 3.532(8) 163.4 8_665 yes
N1 H1A Cl1 0.88 2.68 3.356(10) 134.0 3_556 yes
C6 H6A Cl3 0.99 2.68 3.579(14) 150.6 . yes
C6 H6B Cl2 0.99 2.77 3.632(15) 146.2 . yes
C9 H9 Cl3 0.95 3.05 3.894(10) 149.2 . yes
C10 H10 Cl4 0.95 3.21 3.970(10) 138.5 . yes
N2 H2A Cl2 0.88 2.45 3.144(10) 136.3 3_646 yes
N2 H2A Cl3 0.88 2.72 3.368(11) 131.5 3_546 yes
C11 H11 Cl4 0.95 3.04 3.693(11) 127.4 2_554 yes
C11 H11 Cl1 0.95 2.82 3.439(11) 124.0 3_546 yes
C12 H12 Cl4 0.95 3.09 3.720(11) 124.9 2_554 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C6 -176.6(11) . . . . ?
C2 C1 N1 C5 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C6 C7 179.0(10) . . . . ?
C3 C4 C5 N1 0.0 . . . . ?
C3 C6 C7 C8 177.8(10) . . . . ?
C4 C3 C6 C7 2.5(16) . . . . ?
C4 C5 N1 C1 0.0 . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
C6 C3 C4 C5 176.5(12) . . . . ?
C6 C7 C8 C9 7.3(15) . . . . ?
C6 C7 C8 C12 -173.4(10) . . . . ?
C7 C8 C9 C10 179.3(12) . . . . ?
C7 C8 C12 C11 -179.3(12) . . . . ?
C8 C9 C10 N2 0.0 . . . . ?
C9 C8 C12 C11 0.0 . . . . ?
C9 C10 N2 C11 0.0 . . . . ?
C10 N2 C11 C12 0.0 . . . . ?
N2 C11 C12 C8 0.0 . . . . ?
C12 C8 C9 C10 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nk1224
_database_code_depnum_ccdc_archive 'CCDC 2413119'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-05-15 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
_audit_creation_date             2025-05-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Cl5, I2, C13 H16 N2'
_chemical_formula_sum            'C13 H16 Bi Cl5 I2 N2'
_chemical_formula_weight         840.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3756(3)
_cell_length_b                   18.7195(4)
_cell_length_c                   8.2348(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.2120(10)
_cell_angle_gamma                90
_cell_volume                     2198.49(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8998
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.821
_shelx_estimated_absorpt_T_min   0.233
_exptl_absorpt_coefficient_mu    11.435
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.5581.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.539
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28700
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.529
_diffrn_reflns_theta_min         1.428
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5371
_reflns_number_total             6720
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.815
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.208
_refine_ls_extinction_coef       0.00037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         6720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0169P)²+2.2265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0651
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C9(H9), C7(H7), C10(H10), C2(H2A), C6(H6), C1(H1A), C5(H5),
 C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.75337(2) 0.65074(2) 0.70549(2) 0.01353(5) Uani 1 1 d . . . . .
I1 I 0.64537(2) 0.33873(2) 0.42606(4) 0.02448(8) Uani 1 1 d . . . . .
I2 I 0.83424(2) 0.33075(2) 0.43519(4) 0.02839(9) Uani 1 1 d . . . . .
Cl3 Cl 0.75656(8) 0.53585(6) 0.51650(14) 0.0183(2) Uani 1 1 d . . . . .
Cl4 Cl 0.74146(8) 0.77341(6) 0.89587(15) 0.0252(3) Uani 1 1 d . . . . .
Cl5 Cl 0.93875(8) 0.65656(6) 0.70973(15) 0.0225(2) Uani 1 1 d . . . . .
Cl2 Cl 0.76438(8) 0.57667(6) 0.96782(14) 0.0234(2) Uani 1 1 d . . . . .
Cl1 Cl 0.56366(8) 0.64144(7) 0.64765(16) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.4104(3) 0.4061(2) 0.7628(5) 0.0255(10) Uani 1 1 d . . . . .
H1 H 0.352709 0.408387 0.712512 0.031 Uiso 1 1 calc R U . . .
N2 N 1.0764(3) 0.4117(2) 0.6804(5) 0.0247(9) Uani 1 1 d . . . . .
H2 H 1.120328 0.414911 0.615223 0.030 Uiso 1 1 calc R U . . .
C8 C 0.9390(3) 0.4006(2) 0.8787(5) 0.0163(9) Uani 1 1 d . . . . .
C3 C 0.5904(3) 0.3971(2) 0.9149(5) 0.0174(9) Uani 1 1 d . . . . .
C9 C 0.9922(3) 0.3418(3) 0.8461(6) 0.0226(10) Uani 1 1 d . . . . .
H9 H 0.981475 0.296879 0.894305 0.027 Uiso 1 1 calc R U . . .
C7 C 0.9585(3) 0.4659(3) 0.8088(6) 0.0206(10) Uani 1 1 d . . . . .
H7 H 0.923048 0.507069 0.828987 0.025 Uiso 1 1 calc R U . . .
C10 C 1.0600(4) 0.3482(3) 0.7450(6) 0.0261(11) Uani 1 1 d . . . . .
H10 H 1.095386 0.307565 0.720616 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5232(3) 0.3482(3) 0.9457(6) 0.0248(11) Uani 1 1 d . . . . .
H2A H 0.539492 0.310539 1.021308 0.030 Uiso 1 1 calc R U . . .
C6 C 1.0286(3) 0.4707(3) 0.7110(6) 0.0241(11) Uani 1 1 d . . . . .
H6 H 1.043215 0.515357 0.665392 0.029 Uiso 1 1 calc R U . . .
C1 C 0.4336(4) 0.3530(3) 0.8690(7) 0.0299(12) Uani 1 1 d . . . . .
H1A H 0.387905 0.318827 0.890913 0.036 Uiso 1 1 calc R U . . .
C12 C 0.7643(3) 0.3908(3) 0.8839(6) 0.0205(10) Uani 1 1 d . . . . .
H12A H 0.755933 0.431815 0.807560 0.025 Uiso 1 1 calc R U . . .
H12B H 0.758596 0.346268 0.818539 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8612(3) 0.3944(3) 0.9841(6) 0.0227(10) Uani 1 1 d . . . . .
H11A H 0.863534 0.436089 1.058444 0.027 Uiso 1 1 calc R U . . .
H11B H 0.871109 0.350881 1.052330 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4726(4) 0.4558(3) 0.7309(6) 0.0285(12) Uani 1 1 d . . . . .
H5 H 0.453857 0.493393 0.656570 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5628(3) 0.4525(3) 0.8049(6) 0.0270(11) Uani 1 1 d . . . . .
H4 H 0.606925 0.487715 0.781951 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6893(3) 0.3925(3) 0.9981(6) 0.0235(11) Uani 1 1 d . . . . .
H13A H 0.695396 0.348893 1.066571 0.028 Uiso 1 1 calc R U . . .
H13B H 0.701266 0.434058 1.072176 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl3 2.6585(11) . ?
Bi1 Cl4 2.9046(12) 4_575 ?
Bi1 Cl4 2.7979(12) . ?
Bi1 Cl5 2.6631(11) . ?
Bi1 Cl2 2.5550(12) . ?
Bi1 Cl1 2.7145(12) . ?
I1 I2 2.7109(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.338(7) . ?
N1 C5 1.339(6) . ?
N2 H2 0.8800 . ?
N2 C10 1.336(6) . ?
N2 C6 1.343(6) . ?
C8 C9 1.386(6) . ?
C8 C7 1.395(6) . ?
C8 C11 1.503(6) . ?
C3 C2 1.377(6) . ?
C3 C4 1.401(7) . ?
C3 C13 1.502(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.364(7) . ?
C7 H7 0.9500 . ?
C7 C6 1.370(6) . ?
C10 H10 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C1 1.365(7) . ?
C6 H6 0.9500 . ?
C1 H1A 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.529(6) . ?
C12 C13 1.517(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C4 1.363(7) . ?
C4 H4 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 Bi1 Cl4 83.40(3) . 4_575 ?
Cl3 Bi1 Cl4 177.18(3) . . ?
Cl3 Bi1 Cl5 87.14(3) . . ?
Cl3 Bi1 Cl1 86.34(4) . . ?
Cl4 Bi1 Cl4 95.140(12) . 4_575 ?
Cl5 Bi1 Cl4 95.20(4) . . ?
Cl5 Bi1 Cl4 86.57(4) . 4_575 ?
Cl5 Bi1 Cl1 170.62(4) . . ?
Cl2 Bi1 Cl3 92.99(4) . . ?
Cl2 Bi1 Cl4 88.47(4) . . ?
Cl2 Bi1 Cl4 176.39(4) . 4_575 ?
Cl2 Bi1 Cl5 93.18(4) . . ?
Cl2 Bi1 Cl1 93.89(4) . . ?
Cl1 Bi1 Cl4 91.15(4) . . ?
Cl1 Bi1 Cl4 85.99(4) . 4_575 ?
Bi1 Cl4 Bi1 153.14(5) . 4_576 ?
C1 N1 H1 119.1 . . ?
C1 N1 C5 121.7(4) . . ?
C5 N1 H1 119.1 . . ?
C10 N2 H2 118.7 . . ?
C10 N2 C6 122.5(4) . . ?
C6 N2 H2 118.7 . . ?
C9 C8 C7 118.2(4) . . ?
C9 C8 C11 121.3(4) . . ?
C7 C8 C11 120.5(4) . . ?
C2 C3 C4 117.6(4) . . ?
C2 C3 C13 121.6(4) . . ?
C4 C3 C13 120.8(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
N2 C10 C9 119.8(5) . . ?
N2 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 C3 121.0(5) . . ?
C1 C2 H2A 119.5 . . ?
N2 C6 C7 119.2(5) . . ?
N2 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
N1 C1 C2 119.7(5) . . ?
N1 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C13 C12 C11 109.6(4) . . ?
C8 C11 C12 112.7(4) . . ?
C8 C11 H11A 109.1 . . ?
C8 C11 H11B 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C5 H5 119.9 . . ?
N1 C5 C4 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C13 C12 115.1(4) . . ?
C3 C13 H13A 108.5 . . ?
C3 C13 H13B 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Cl3 0.88 2.52 3.293(4) 146.4 3_666 yes
N2 H2 Cl3 0.88 2.37 3.215(4) 159.6 3_766 yes
C10 H10 Cl4 0.95 2.72 3.505(5) 140.5 2_746 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C4 C3 -0.2(8) . . . . ?
C8 C9 C10 N2 1.5(7) . . . . ?
C8 C7 C6 N2 1.6(7) . . . . ?
C3 C2 C1 N1 -0.2(8) . . . . ?
C9 C8 C7 C6 -0.1(7) . . . . ?
C9 C8 C11 C12 -100.8(5) . . . . ?
C7 C8 C9 C10 -1.5(7) . . . . ?
C7 C8 C11 C12 78.1(6) . . . . ?
C10 N2 C6 C7 -1.7(7) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C2 C3 C13 C12 125.4(5) . . . . ?
C6 N2 C10 C9 0.1(7) . . . . ?
C1 N1 C5 C4 1.3(8) . . . . ?
C11 C8 C9 C10 177.4(4) . . . . ?
C11 C8 C7 C6 -179.0(4) . . . . ?
C11 C12 C13 C3 173.8(4) . . . . ?
C5 N1 C1 C2 -1.1(8) . . . . ?
C4 C3 C2 C1 1.2(7) . . . . ?
C4 C3 C13 C12 -55.8(6) . . . . ?
C13 C3 C2 C1 -179.9(5) . . . . ?
C13 C3 C4 C5 -179.9(5) . . . . ?
C13 C12 C11 C8 -174.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3_300k
_database_code_depnum_ccdc_archive 'CCDC 2426310'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-05-15 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
_audit_creation_date             2025-05-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I2, Cl5 Sb, C13 H16 N2'
_chemical_formula_sum            'C13 H16 Cl5 I2 N2 Sb'
_chemical_formula_weight         753.08
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.3811(12)
_cell_length_b                   14.2816(11)
_cell_length_c                   9.9869(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2193.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2792
_cell_measurement_temperature    274.00
_cell_measurement_theta_max      77.09
_cell_measurement_theta_min      5.28
_shelx_estimated_absorpt_T_max   0.211
_shelx_estimated_absorpt_T_min   0.133
_exptl_absorpt_coefficient_mu    37.675
_exptl_absorpt_correction_T_max  0.2166
_exptl_absorpt_correction_T_min  0.0886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1222 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.4090.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.280
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12734
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.933
_diffrn_reflns_theta_min         5.281
_diffrn_ambient_temperature      274.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2047
_reflns_number_total             2398
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.00034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.7315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.64295(2) 0.65493(3) 0.42946(3) 0.06569(13) Uani 1 1 d . . . . .
Sb1 Sb 0.91845(2) 0.750000 0.89673(3) 0.04915(13) Uani 1 2 d S T P . .
Cl1 Cl 0.90513(9) 0.56674(9) 0.89223(13) 0.0707(3) Uani 1 1 d . . . . .
Cl2 Cl 0.77736(12) 0.750000 1.07730(13) 0.0634(4) Uani 1 2 d S T P . .
Cl3 Cl 0.80409(9) 0.750000 0.73390(12) 0.0509(3) Uani 1 2 d S T P . .
Cl4 Cl 1.02539(10) 0.750000 0.71178(17) 0.0656(4) Uani 1 2 d S T P . .
N1 N 0.8165(3) 0.4201(3) 0.4379(5) 0.0698(11) Uani 1 1 d . . . . .
H1 H 0.785928 0.370967 0.453893 0.084 Uiso 1 1 calc R U . . .
C1 C 0.8346(4) 0.4412(4) 0.3126(6) 0.0764(14) Uani 1 1 d . . . . .
H1A H 0.814493 0.403152 0.243747 0.092 Uiso 1 1 calc R U . . .
C2 C 0.8827(3) 0.5185(4) 0.2838(5) 0.0665(12) Uani 1 1 d . . . . .
H2 H 0.895825 0.533216 0.195316 0.080 Uiso 1 1 calc R U . . .
C3 C 0.9120(3) 0.5754(3) 0.3869(5) 0.0547(10) Uani 1 1 d . . . . .
C4 C 0.8920(3) 0.5500(3) 0.5176(5) 0.0602(11) Uani 1 1 d . . . . .
H4 H 0.911480 0.586215 0.588963 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8435(3) 0.4716(4) 0.5404(5) 0.0677(12) Uani 1 1 d . . . . .
H5 H 0.829507 0.454262 0.627540 0.081 Uiso 1 1 calc R U . . .
C6 C 0.9618(3) 0.6624(3) 0.3595(6) 0.0691(13) Uani 1 1 d . . . . .
H6A H 0.981388 0.661571 0.267137 0.083 Uiso 1 1 calc R U . . .
H6B H 1.012905 0.663696 0.416354 0.083 Uiso 1 1 calc R U . . .
C7 C 0.9094(4) 0.750000 0.3832(6) 0.0503(13) Uani 1 2 d S T P . .
H7A H 0.859412 0.750000 0.323942 0.060 Uiso 1 2 calc R U P . .
H7B H 0.888144 0.750000 0.474609 0.060 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I1 2.7155(8) 7_575 ?
Sb1 Cl1 2.6256(13) 7_575 ?
Sb1 Cl1 2.6256(13) . ?
Sb1 Cl2 2.8217(17) . ?
Sb1 Cl3 2.3955(13) . ?
Sb1 Cl4 2.4734(16) . ?
N1 H1 0.8600 . ?
N1 C1 1.316(7) . ?
N1 C5 1.328(7) . ?
C1 H1A 0.9300 . ?
C1 C2 1.360(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(7) . ?
C3 C4 1.389(6) . ?
C3 C6 1.485(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(7) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.507(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Sb1 Cl1 170.83(6) . 7_575 ?
Cl1 Sb1 Cl2 87.19(3) 7_575 . ?
Cl1 Sb1 Cl2 87.19(3) . . ?
Cl3 Sb1 Cl1 86.05(3) . 7_575 ?
Cl3 Sb1 Cl1 86.05(3) . . ?
Cl3 Sb1 Cl2 82.48(5) . . ?
Cl3 Sb1 Cl4 88.93(5) . . ?
Cl4 Sb1 Cl1 92.24(3) . . ?
Cl4 Sb1 Cl1 92.24(3) . 7_575 ?
Cl4 Sb1 Cl2 171.41(5) . . ?
C1 N1 H1 118.7 . . ?
C1 N1 C5 122.7(5) . . ?
C5 N1 H1 118.7 . . ?
N1 C1 H1A 119.9 . . ?
N1 C1 C2 120.2(5) . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 118.2(5) . . ?
C2 C3 C6 121.3(5) . . ?
C4 C3 C6 120.4(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 119.8(5) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C6 H6A 109.0 . . ?
C3 C6 H6B 109.0 . . ?
C3 C6 C7 112.9(4) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 C6 112.2(5) 7_575 . ?
C6 C7 H7A 109.2 7_575 . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 7_575 . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Cl2 0.86 2.33 3.151(5) 158.5 2_664 yes
C1 H1A Cl3 0.93 2.85 3.554(6) 133.4 2_664 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.5(8) . . . . ?
C1 N1 C5 C4 0.2(8) . . . . ?
C1 C2 C3 C4 1.0(7) . . . . ?
C1 C2 C3 C6 -177.7(5) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C2 C3 C6 C7 106.7(6) . . . . ?
C3 C4 C5 N1 0.4(7) . . . . ?
C3 C6 C7 C6 178.0(3) . . . 7_575 ?
C4 C3 C6 C7 -71.9(6) . . . . ?
C5 N1 C1 C2 -0.1(8) . . . . ?
C6 C3 C4 C5 177.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_nk1198
_database_code_depnum_ccdc_archive 'CCDC 2413117'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-05-22 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
_audit_creation_date             2025-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Cl5, I2, C12 H14 N2'
_chemical_formula_sum            'C12 H14 Bi Cl5 I2 N2'
_chemical_formula_weight         826.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   7.4735(2)
_cell_length_b                   14.2835(4)
_cell_length_c                   19.7322(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2106.37(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8671
_cell_measurement_temperature    220.00
_cell_measurement_theta_max      31.47
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.755
_shelx_estimated_absorpt_T_min   0.154
_exptl_absorpt_coefficient_mu    11.933
_exptl_absorpt_correction_T_max  0.3728
_exptl_absorpt_correction_T_min  0.1658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1396 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.4447.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.606
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27777
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.508
_diffrn_reflns_theta_min         2.064
_diffrn_ambient_temperature      220.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3007
_reflns_number_total             3616
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.022
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       0.00195(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²+0.6520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 Bi1-Cl1A \\sim Bi1-Cl1B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C6, C3, C4, C2, C5, C1, C7, N1, C8, C9, C12, C10, C11, N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Cl1B)=0.5*(1-FVAR(2))
 Sof(Cl1A)=0.5*FVAR(2)
 Fixed Sof: C3(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5) N1(0.5) H1(0.5) C1(0.5)
 H1A(0.5) C2(0.5) H2(0.5) C8(0.5) C9(0.5) H9(0.5) C10(0.5) H10(0.5) N2(0.5)
 H2A(0.5) C11(0.5) H11(0.5) C12(0.5) H12(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5)
 H7A(0.5) H7B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), N1(H1), C1(H1A), C2(H2), C9(H9), C10(H10), N2(H2A), C11(H11),
 C12(H12)
5.c Fitted hexagon refined as free rotating group:
 C8(C9,C10,N2,C11,C12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.76976(2) 0.750000 -0.14167(2) 0.02088(6) Uani 1 2 d DS T P . .
I1 I 0.23815(3) 0.65490(2) 0.12354(2) 0.03163(7) Uani 1 1 d . . . . .
Cl2 Cl 0.49742(14) 0.750000 -0.05969(6) 0.0312(2) Uani 1 2 d S T P A .
Cl3 Cl 1.01145(14) 0.750000 -0.04901(6) 0.0294(2) Uani 1 2 d S T P A .
Cl4 Cl 0.76613(13) 0.56190(7) -0.13535(6) 0.0450(2) Uani 1 1 d . . . . .
Cl1A Cl 1.0717(12) 0.750000 -0.2304(7) 0.042(3) Uani 0.65(7) 2 d DS T P A 1
C3 C 0.7367(13) 0.6134(6) 0.1143(4) 0.0217(16) Uani 0.5 1 d . . P B -1
C4 C 0.7343(16) 0.5760(7) 0.1766(5) 0.035(2) Uani 0.5 1 d . . P B -1
H4 H 0.729057 0.615484 0.214690 0.042 Uiso 0.5 1 calc R U P B -1
C5 C 0.739(2) 0.4817(8) 0.1855(6) 0.045(3) Uani 0.5 1 d . . P B -1
H5 H 0.740302 0.455536 0.229204 0.053 Uiso 0.5 1 calc R U P B -1
N1 N 0.743(2) 0.4281(6) 0.1318(5) 0.035(2) Uani 0.5 1 d . . P B -1
H1 H 0.746656 0.367765 0.137609 0.042 Uiso 0.5 1 calc R U P B -1
C1 C 0.7411(19) 0.4606(7) 0.0697(6) 0.042(3) Uani 0.5 1 d . . P B -1
H1A H 0.741986 0.419536 0.032501 0.050 Uiso 0.5 1 calc R U P B -1
C2 C 0.7379(15) 0.5536(6) 0.0604(5) 0.034(2) Uani 0.5 1 d . . P B -1
H2 H 0.736557 0.577924 0.016119 0.041 Uiso 0.5 1 calc R U P B -1
C8 C 0.7356(12) 0.8860(4) 0.1411(4) 0.0235(16) Uani 0.5 1 d G . P B -1
C9 C 0.7497(14) 0.9143(5) 0.0739(3) 0.043(2) Uani 0.5 1 d G . P B -1
H9 H 0.757672 0.869389 0.039229 0.051 Uiso 0.5 1 calc R U P B -1
C10 C 0.7519(18) 1.0091(6) 0.0580(3) 0.057(4) Uani 0.5 1 d G . P B -1
H10 H 0.761391 1.028290 0.012569 0.068 Uiso 0.5 1 calc R U P B -1
N2 N 0.740(2) 1.0756(4) 0.1093(5) 0.049(3) Uani 0.5 1 d G . P B -1
H2A H 0.741398 1.134894 0.099314 0.058 Uiso 0.5 1 calc R U P B -1
C11 C 0.726(2) 1.0472(5) 0.1764(4) 0.056(4) Uani 0.5 1 d G . P B -1
H11 H 0.717909 1.092146 0.211118 0.067 Uiso 0.5 1 calc R U P B -1
C12 C 0.7237(16) 0.9524(5) 0.1924(3) 0.044(3) Uani 0.5 1 d G . P B -1
H12 H 0.714190 0.933245 0.237779 0.052 Uiso 0.5 1 calc R U P B -1
C6 C 0.7364(7) 0.7177(4) 0.1002(4) 0.0292(13) Uani 0.5 1 d . . P B -1
H6A H 0.842690 0.732162 0.073038 0.035 Uiso 0.5 1 calc R U P B -1
H6B H 0.631674 0.731776 0.072121 0.035 Uiso 0.5 1 calc R U P B -1
C7 C 0.7342(8) 0.7828(4) 0.1594(4) 0.0296(13) Uani 0.5 1 d . . P B -1
H7A H 0.838709 0.769544 0.187859 0.036 Uiso 0.5 1 calc R U P B -1
H7B H 0.627157 0.769858 0.186537 0.036 Uiso 0.5 1 calc R U P B -1
Cl1B Cl 1.028(7) 0.7656(15) -0.247(2) 0.062(6) Uani 0.17(3) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl2 2.5999(11) . ?
Bi1 Cl3 2.5701(10) . ?
Bi1 Cl4 2.6898(10) . ?
Bi1 Cl4 2.6898(10) 7_575 ?
Bi1 Cl1A 2.927(8) 6 ?
Bi1 Cl1A 2.856(6) . ?
Bi1 Cl1B 2.856(11) 6 ?
Bi1 Cl1B 2.856(11) 4_464 ?
Bi1 Cl1B 2.842(11) . ?
Bi1 Cl1B 2.842(11) 7_575 ?
I1 I1 2.7168(5) 7_575 ?
C3 C4 1.342(11) . ?
C3 C2 1.364(11) . ?
C3 C6 1.516(10) . ?
C4 H4 0.9400 . ?
C4 C5 1.359(12) . ?
C5 H5 0.9400 . ?
C5 N1 1.307(13) . ?
N1 H1 0.8700 . ?
N1 C1 1.310(13) . ?
C1 H1A 0.9400 . ?
C1 C2 1.342(11) . ?
C2 H2 0.9400 . ?
C8 C9 1.3900 . ?
C8 C12 1.3900 . ?
C8 C7 1.518(8) . ?
C9 H9 0.9400 . ?
C9 C10 1.3900 . ?
C10 H10 0.9400 . ?
C10 N2 1.3900 . ?
N2 H2A 0.8700 . ?
N2 C11 1.3900 . ?
C11 H11 0.9400 . ?
C11 C12 1.3900 . ?
C12 H12 0.9400 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 C7 1.493(10) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
Cl1B Cl1B 0.44(4) 7_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Bi1 Cl4 87.89(2) . . ?
Cl2 Bi1 Cl4 87.89(2) . 7_575 ?
Cl2 Bi1 Cl1A 179.3(3) . . ?
Cl2 Bi1 Cl1A 98.1(3) . 6 ?
Cl2 Bi1 Cl1B 89.0(13) . 6 ?
Cl2 Bi1 Cl1B 170.3(12) . 7_575 ?
Cl2 Bi1 Cl1B 170.3(12) . . ?
Cl2 Bi1 Cl1B 89.0(13) . 4_464 ?
Cl3 Bi1 Cl2 96.18(4) . . ?
Cl3 Bi1 Cl4 88.52(2) . . ?
Cl3 Bi1 Cl4 88.52(2) . 7_575 ?
Cl3 Bi1 Cl1A 165.7(3) . 6 ?
Cl3 Bi1 Cl1A 83.2(3) . . ?
Cl3 Bi1 Cl1B 173.1(11) . 4_464 ?
Cl3 Bi1 Cl1B 173.1(11) . 6 ?
Cl3 Bi1 Cl1B 92.5(13) . . ?
Cl3 Bi1 Cl1B 92.5(13) . 7_575 ?
Cl4 Bi1 Cl4 174.56(5) . 7_575 ?
Cl4 Bi1 Cl1A 92.00(2) 7_575 6 ?
Cl4 Bi1 Cl1A 92.00(2) . 6 ?
Cl4 Bi1 Cl1A 92.09(2) 7_575 . ?
Cl4 Bi1 Cl1A 92.09(2) . . ?
Cl4 Bi1 Cl1B 87.2(4) 7_575 6 ?
Cl4 Bi1 Cl1B 96.8(4) . . ?
Cl4 Bi1 Cl1B 87.2(4) . 4_464 ?
Cl4 Bi1 Cl1B 87.9(4) 7_575 . ?
Cl4 Bi1 Cl1B 96.1(4) 7_575 4_464 ?
Cl4 Bi1 Cl1B 96.1(4) . 6 ?
Cl4 Bi1 Cl1B 96.8(4) 7_575 7_575 ?
Cl4 Bi1 Cl1B 87.9(4) . 7_575 ?
Cl1A Bi1 Cl1A 82.58(5) . 6 ?
Cl1A Bi1 Cl1B 91.6(11) . 6 ?
Cl1A Bi1 Cl1B 91.6(11) . 4_464 ?
Cl1B Bi1 Cl1B 82.01(6) 7_575 4_464 ?
Cl1B Bi1 Cl1B 9.0(9) 7_575 . ?
Cl1B Bi1 Cl1B 82.72(8) . 4_464 ?
Bi1 Cl1A Bi1 158.2(6) . 6_655 ?
C4 C3 C2 117.8(8) . . ?
C4 C3 C6 124.0(8) . . ?
C2 C3 C6 118.2(8) . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(8) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.8 . . ?
N1 C5 C4 118.5(9) . . ?
N1 C5 H5 120.8 . . ?
C5 N1 H1 118.3 . . ?
C5 N1 C1 123.4(9) . . ?
C1 N1 H1 118.3 . . ?
N1 C1 H1A 120.7 . . ?
N1 C1 C2 118.6(10) . . ?
C2 C1 H1A 120.7 . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.8(9) . . ?
C1 C2 H2 119.6 . . ?
C9 C8 C12 120.0 . . ?
C9 C8 C7 120.7(5) . . ?
C12 C8 C7 119.3(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 N2 120.0 . . ?
N2 C10 H10 120.0 . . ?
C10 N2 H2A 120.0 . . ?
C11 N2 C10 120.0 . . ?
C11 N2 H2A 120.0 . . ?
N2 C11 H11 120.0 . . ?
N2 C11 C12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C8 C12 H12 120.0 . . ?
C11 C12 C8 120.0 . . ?
C11 C12 H12 120.0 . . ?
C3 C6 H6A 107.8 . . ?
C3 C6 H6B 107.8 . . ?
H6A C6 H6B 107.2 . . ?
C7 C6 C3 117.9(6) . . ?
C7 C6 H6A 107.8 . . ?
C7 C6 H6B 107.8 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 C8 114.7(6) . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
Bi1 Cl1B Bi1 170.4(13) . 6_655 ?
Cl1B Cl1B Bi1 85.5(4) 7_575 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 Cl4 0.94 2.68 3.590(11) 161.9 2_665 yes
N2 H2A Cl2 0.87 2.55 3.211(10) 133.6 3_655 yes
N2 H2A Cl3 0.87 2.66 3.327(10) 133.9 3_755 yes
C11 H11 Cl4 0.94 3.06 3.720(8) 128.4 8_766 yes
C12 H12 Cl4 0.94 3.11 3.743(6) 126.3 8_766 yes
C6 H6A Cl3 0.98 2.73 3.620(7) 151.2 . yes
C6 H6B Cl2 0.98 2.80 3.655(7) 146.2 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C5 N1 -1.4(14) . . . . ?
C3 C6 C7 C8 179.5(5) . . . . ?
C4 C3 C2 C1 -1.6(13) . . . . ?
C4 C3 C6 C7 0.3(11) . . . . ?
C4 C5 N1 C1 -0.3(15) . . . . ?
C5 N1 C1 C2 1.0(16) . . . . ?
N1 C1 C2 C3 0.0(14) . . . . ?
C2 C3 C4 C5 2.3(13) . . . . ?
C2 C3 C6 C7 179.7(7) . . . . ?
C8 C9 C10 N2 0.0 . . . . ?
C9 C8 C12 C11 0.0 . . . . ?
C9 C8 C7 C6 -3.9(8) . . . . ?
C9 C10 N2 C11 0.0 . . . . ?
C10 N2 C11 C12 0.0 . . . . ?
N2 C11 C12 C8 0.0 . . . . ?
C12 C8 C9 C10 0.0 . . . . ?
C12 C8 C7 C6 176.5(6) . . . . ?
C6 C3 C4 C5 -178.3(10) . . . . ?
C6 C3 C2 C1 178.9(9) . . . . ?
C7 C8 C9 C10 -179.6(8) . . . . ?
C7 C8 C12 C11 179.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
